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US2381852A - Treatment of textiles - Google Patents

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Publication number
US2381852A
US2381852A US43483242A US2381852A US 2381852 A US2381852 A US 2381852A US 43483242 A US43483242 A US 43483242A US 2381852 A US2381852 A US 2381852A
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Prior art keywords
acid
salt
water
process
succinic
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Carroll A Hochwalt
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192Polycarboxylic acids; Anhydrides, halides or salts thereof
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/907Resistant against plant or animal attack
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2938Coating on discrete and individual rods, strands or filaments
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2213Coating or impregnation is specified as weather proof, water vapor resistant, or moisture resistant

Description

l i i lllt'a' ls'e 05 MTRQQ are Patented Aug.

assignor to Monsanto 7 N Drawing. Applica Serial No.

6 Claims. (Cl

This invention relates to a process for the treatment of,fihrp,u s materials and more specifically to a process whereby textiles are simultaneously protected from attack by, f.ungiand corporation of Delaware s PATENT OFFICE Q TREATMENT OF TEXTILES Carroll A. Hochwalt, Montgomery County, Ohio,

Chemical Company, a

tion March 16,1942, 4 l I alkaline. (3) It must be insoluble or only slightly soluble in water to avoid leaching out by rain. (4) It should not increase inflammability. (5) It should not detract from fiber strength. (6) It bacteria and rendered moisture-proof, 5 must be readily available and easily applied. vMuch damage is caused to fibrous materials by (7) It should not cause excessive shrinkage. fungi and bacteria. Mildew, that is, the growth (8) It should not unfavorably affect the feel of of fungi on fibrous media, is characterized by disthe material treated. I coloration of the media and the development of An object of the present invention is the proa musty smell accompanied by decay or rotting l0 vision of new textile treating processes and prodof the fiber. This is caused by utilization of ceructs whereby there are used fungicidal and bactain constituents of the fiber in the metabolic tericidal materials having particularly desirable processes of fungi and bacteria, and is usually qualities, Another object of the present invencharacterized by loss of strength of the fiber. tion is the provision of aprocess whereby textiles Since the main factors determining microare simultaneously protected from attack by biological growth are food and moisture, and fungi and bacteria and at the same time rendered since the cellulose of cotton, hemp, jute, etc., and moisture-proof and water repellent, Other obthe protein, fat and gum constituents of wool jects and advantageswillhereinafter become apand silk provide ready food for fungi and bacteria parent. these fibers and textile materials made there- By the process of the present invention a from may be readily attacked by such microfibrous material, for example, cotton cloth, may organisms under proper moisture conditions. first be treated with an aliphatic dibasic acid or Storage of fibrous materials in damp warehouses, anhydride or salt thereof having as a substituent exposure to rain without immediate drying, as in an olefinic hydrocarbon residue of from 5 to 16 the case of tents, tarpaulins, awnings, etc., and carbon atoms and then with a water soluble cop- I use of fibrous materials,for example, fish nets, I per salt. The alkylene, e. g., amylene, hexylene, under conditions of constant wetting provide heptylene, octylene, ii ty n tri sc v en favorable moisture conditions for the growth of or tetraisobutylene, substituted dibasic acids or fiber-destroying fungi and bacteria. anhydrides used may be prepared by reaction The problem of protecting fibrous materials of a salt of an unsatm'ated dibasic acid or by against the attack of these microorganisms has reaction of the anhydride with an aliphatic hybeen complicated by certain stringent requiredrccarbcn h v an o efi double o as dements. The mere gross surface application of scribed in U. S. Patent 2,055,456 to Eichwald. substances possessin fungicidal and bactericidal Such alkylene substituted acids or anhydrides are properties is often inadequate in that it does not relatively insoluble in Waller and for the p p prevent attack by microorganisms which may of expediting their application to the cellulosic j have been previously deposited within the fiber. material I may convert them by known methods The impregnation of fibrous materials with fungito their water-soluble alkali metal salts whereby cides and bactericides often results in the impair- I operate by first treating the cellulosic material ment of the strength of the fibrous material by 40 with the aqueous solution of the a lf ilillletalalt the impregnating agent. Again, an otherwise i of the alkylene dibasic acid then with a solution satisfactory impregnating agent may be unsuitof the soluble copperisalt. If desired, however, I able for many purposes in that it may be readily may treat the fibrous material by a one-step leached out of the treated material by rain,-by process wherein I first prepare the relatively washing, etc. water-insoluble copper salt of the alkylene di- The following properties may be considered as basic acid and apply it to the cellulosic material, being desirable in a fungicidal and bactericidal for example, in the form of an aqueous dispersion material for the treatment of textiles: (1) It prepared with the aid of a dispersing agent.

must possess both fungicidal and bactericidal Thus my invention includes the production of properties. (2) It should be neither acid nor copper salts (cupric or cuprous) of alkylene 2 3 d l 53 E 2.

QT- f- "Q LN (Mu "$0 VUI VII succinic acids, such salts having the probable constitution:

where R is an alkylene residue, of from to 1! carbonato'ms- .1 X Q In practice I may operate as follows: I' treat a textile material, for example, cotton cloth, in a padding machine at room temperature for" from 5 to minutes in, say, a 1% to aqueous solution of an alkali metal salt of triisobutylene succinic acid, dry the cloth at approximately 90 C. padding machine with, say, a 1% to 5% aqueous solution of cupric acetate. After a short rinse I in a draft oven, and then treat itin a' Example 1 and then baked for one hour at- 150 C. The atreated cloth will be found to have permanent,

water-resistant fungicidal and bactericidal properties, water-repellency and good feel. Its inflammability will not have been increased, and

its tensile strength will not have been impaired by the treatment.

air-dry the cloth and may then bake it for from 10 to minutes at 120 to 160 C. (5 The effect of the treatment of fabrics by the present process upon change in tensile strength, may be determined by th method described in the American Society for Testing Materials Book of Standards for 1939, part III on pages 364 and 372. Breaking strengths as determined by means of a Model J-2 Scott Tester, using American Society for Testing Materials Specification D39-36 raveled strip method, as described on these pages, indicate that cloths treated according to the process of this invention undergo substantially no change in tensile strength.

1 Fabrics treated according to the process may also be evaluated as to fungus resistance by inoculating them with a culture of Chaetomium globosum, one of the most destructiv of the fiber-attacking fungi, and allowing the so inoculated fabric to stand for two weeks under favorable conditions for growth. Since attack by the fungus results in loss of tensile strength, the effect of th innoculated Chaetomium globosum upon the fabric may be readily estimated by measuring the tensile strength of the fabric before inoculation and after the two-week exposure. Cloths treated according to the process of this invention show substantially no loss of tensile strength after inoculation and exposure to the fungus as above described.

The water repellency of the fabrics treated by the herein described process may be evaluated by two tests applied by those skilled in the art. These tests are known as the spray test and as the hydrostatic head test. Thespray test which I employ is described in the American Dyestuffs Reporter, vol. 28, page 285 for 1939. The hydrostatic head test is described in the 1940 Yearbook of the American Association of Textil Chemists and Colorists at pages 223- 1.

- fungus.

The cloth was found to have a tensile streng of 43.3 pounds as measured on the Scott tester, before inoculation and a tensile strength of 43.6

pounds after inoculation and exposure for two weeks under conditions favoring growth of the .Thus the cloth suffered no loss of strength due toexposure to moisture andfungicidal action. fl, [The treated cloth showed the following degree of water-procfness: Tested with the spray test above referred to, I obtained a moisture absorption of 32.1% and a. hydrostatic head value of 21.2 cm., which Values indicate good water-resistance.

The procedure is that of Example 1, except that instead of using a 1% solution, there is used a 5% solution of triisobutylene succinic anhydride'in benzene. When the treated cloth was evaluated for fungicidal property as described herein, the tensile strength of the cloth after exposure to the fungus was found to be 44.0 pounds-as against 43.1 pounds, the value obtained for the cloth before inoculation.

The treated cloth of this example showed the following degree of water-proofness. Tested with the spray test and the hydrostatic head test above referred to, I obtained a moisture absorption of 28.2% and a hydrostatic head value of 21.2

Instead of the triisobutylene succinic anhydride of the above examples I may use the triisobutylene succinic acid, itself. Moreover when operating in a, non-aqueous media I may use benzene as the solvent or I may use any other inert 1 diluent, as will be understood by those skilled in the art. If it is desired to operate in an aqueous media, I may prepare, say, the disodium salt of triisobutylene succinic acid and apply it to the cellulosic material in the form of, say, a 2% to 20% aqueous solution. Textiles treated with such aqueous solutions of disodium triisobutylene succinate when submitted to subsequent treatment with a 1% to 5% aqueous solution of cupric acetate show the incorporation therein of from I 0.35% to 1.3% copper, based on the weight of the dry textile.

Although the above examples illustrate the operation of this invention by a two-step process, the formation of the copper salt of triisobutylene succinic acid being advantageously precipitated directly upon the fiber, I may likewise operate by a one-step process, by first preparing the copper salt, for example by reaction of the triisobutylene succinic acid with cupric or cuprous acetate, and then applyingit to the textile material. Cupric triisobutylene succinate, for example, may be applied to the cellulosic material by preparing an aqueous dispersion of the salt. While such a dispersion can be prepared mechanically, its preparation is somewhat easier if the cupric triisobutylene succinate is dispersed in the presence of dispersing agents such as copolymers of styrene and maleic anhydride, which copolymers have been converted to their water-soluble salts.

Instead of using triisobutylene succinic acid or its salts for the purpose of the present invention, I may likewise use the alkylene substituted succinic acids or their salts prepared by reaction of such olefinic hydrocarbons as amylene, hexylene, octene, dodecene, etc., with maleic acid or maleic 'anhydride, the use of such alkalene succinic acids according to the present invention likewise resulting in rendering fungicidal, bactericidal and moisture-proof properties 7 to cellulosic materials. Although I prefer to employ the products obtained from maleic acid or its anhydride because these compounds are readily available on a commercial scale, I may likewise use the other alkylene derivatives of aliphatic dibasic acids described in U. S. Patent 2,055,456, for example the products obtained by reaction of olefinic hydrocarbons containing from 5 to 16 carbon atoms with such acids as fumaric acid, citraconic acid or itaconic acid.

What I claim is:

1. The compound having the formula:

where R is an alkylene residue of from 5 to 16 carbon atoms.

2. A textile fiber, the surfaces of which 'contain the cupric salt of an acid of the formula:

i HOOCC-R Hoo0c l-H H where R is an alkylene residue of from 5 to 16 carbon atoms.

3. The process of treating textile fibers to render the same water-repellent and resistant to rot development, comprising treating said fibers with a mono-alkylene succinic acid salt, the alkylene group of which contains from 5 to 16 carbon atoms and thereafter treating said fibers with a soluble cupric salt.

- 4. The process defined in claim 3 in which the soluble copper salt is cupric acetate.

5. The process of treating textile fiber to render the same water repellent and also resistant to the development of fungus organisms of the character of Chaetomium globosum, which comprises treating said fiber with an aqueous solution of the disodium salt of triisobutylene succinic acid, thereupon treating said fibers with a solution of a soluble copper salt and then drying said fibers.

6. A fibrous textile product, the fibers of which carry sufiicient of the cupric salt of triisobutylene succinic acid,'so that said product in the dry state contains from 0.35% to 1.3% of copper.

CARROLL A. HOCHWALT.

US2381852A 1942-03-16 1942-03-16 Treatment of textiles Expired - Lifetime US2381852A (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2471261A (en) * 1946-05-09 1949-05-24 American Cyanamid Co Mildew-proofing
US2655460A (en) * 1949-12-01 1953-10-13 Allied Chem & Dye Corp Dibasic silver salts of alkenyl sucicinic acids and method for combating fungus infestations therewith
US2655461A (en) * 1949-12-01 1953-10-13 Allied Chem & Dye Corp Complex zinc- and silver-ammonia salts of alkenyl succinic acids, methods for preparing them, and method for combating fungi therewith
US2692204A (en) * 1952-07-08 1954-10-19 Nuodex Products Co Inc Organo-mercury dicarboxylate microbicides
US2881097A (en) * 1956-02-02 1959-04-07 Harshaw Chem Corp Mildewcide and flameproofing composition and products produced therefrom
US2903382A (en) * 1958-06-23 1959-09-08 Armour & Co Treatment of fabric with alkenylsuccinic acids and anhydrides to impart water repellency
US3018196A (en) * 1959-12-04 1962-01-23 Olin Mathieson Treatment of cellulosic materials to resist fungicidal attack
US4259383A (en) * 1978-06-30 1981-03-31 Sterling Drug Inc. Disinfecting tissue
US4715980A (en) * 1986-03-17 1987-12-29 Diversey Wyandotte Corporation Antimicrobial sanitizing composition containing n-alkyl and n-alkenyl succinic acid and methods for use
US20080233820A1 (en) * 2007-03-23 2008-09-25 Pompeo Michael P Method of treating burlap

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2471261A (en) * 1946-05-09 1949-05-24 American Cyanamid Co Mildew-proofing
US2655460A (en) * 1949-12-01 1953-10-13 Allied Chem & Dye Corp Dibasic silver salts of alkenyl sucicinic acids and method for combating fungus infestations therewith
US2655461A (en) * 1949-12-01 1953-10-13 Allied Chem & Dye Corp Complex zinc- and silver-ammonia salts of alkenyl succinic acids, methods for preparing them, and method for combating fungi therewith
US2692204A (en) * 1952-07-08 1954-10-19 Nuodex Products Co Inc Organo-mercury dicarboxylate microbicides
US2881097A (en) * 1956-02-02 1959-04-07 Harshaw Chem Corp Mildewcide and flameproofing composition and products produced therefrom
US2903382A (en) * 1958-06-23 1959-09-08 Armour & Co Treatment of fabric with alkenylsuccinic acids and anhydrides to impart water repellency
US3018196A (en) * 1959-12-04 1962-01-23 Olin Mathieson Treatment of cellulosic materials to resist fungicidal attack
US4259383A (en) * 1978-06-30 1981-03-31 Sterling Drug Inc. Disinfecting tissue
US4715980A (en) * 1986-03-17 1987-12-29 Diversey Wyandotte Corporation Antimicrobial sanitizing composition containing n-alkyl and n-alkenyl succinic acid and methods for use
US20080233820A1 (en) * 2007-03-23 2008-09-25 Pompeo Michael P Method of treating burlap

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